


Let Me Please You

by MarmeLady_Orange



Series: The Craigslist Experiment [1]
Category: Supernatural
Genre: Alternate Universe- No Supernatural, Anal Fingering, Anal Sex, Angst and Fluff and Smut, Bisexuality, Blow Jobs, Castiel and Dean Winchester are Switches, Castiel is a little too proper, College Student Jessica, College Student Sam, Complete, Dean is insecure, Dean tries gay sex for the first time, Internet Hookup, Jessica is kinda filling Charlie’s shoes in this piece, Language, M/M, Male Homosexuality, Mechanic Dean, One Shot, Rimming, Sexual Experimentation, They’re perfect for each other, Writer Castiel
Language: English
Status: Completed
Published: 2015-03-02
Updated: 2015-03-02
Packaged: 2018-03-16 01:55:57
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 18,563
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3470096
Author URL: https://archiveofourown.org/users/MarmeLady_Orange/pseuds/MarmeLady_Orange
Summary: <blockquote class="userstuff">
              <p>Dean liked to read the casual encounter ads on Craigslist. He really did. Not that he ever intended on answering any of them. </p><p>Then one caught his attention…</p><p>***</p><p>IF YOU WANT TO READ THE RUSSIAN TRANSLATION, YOU CAN FIND IT <a href="https://ficbook.net/readfic/4212706">HERE.</a></p>
            </blockquote>





	Let Me Please You

**Author's Note:**

  * Translation into Русский available: [Все для тебя](https://archiveofourown.org/works/7134035) by [FoggyFeline71](https://archiveofourown.org/users/FoggyFeline71/pseuds/FoggyFeline71)



> I swear… this started as a pure, 100% smut piece. There wasn’t supposed to be feeeeeelings (cue Crowley) or anything but our two delectable men going at it.
> 
> Once again, it got away from me. It can never be only about sex with these two, however hard I try. Unless they’d already be in a relationship, I guess.
> 
> So now, instead of a 2500-5000 words little thing, it turned into an 18k monster. I can only hope that it was worth all the extra work. ;)
> 
> Also… I did a little drawing… it is safe to say that both the drawing and the writing inspired one another… I hope you’ll like it.
> 
>  
> 
> .

   

_‘Well, this is intriguing,’_ Dean thought as he read the ad. 

He had taken a habit of browsing through Craigslist’s casual encounters listings for some time now. He’d never answered to any of them, of course. If asked, he would have explained that he liked to read them as they often were hilarious. That was before that very Saturday morning. For the first time, he felt the urge to respond.

At twenty-eight years old, Dean knew for sure that he wasn’t gay. And he couldn’t consider himself bisexual either, not yet anyway. What he knew for sure was that he had been curious enough to wonder. And the older he got, the more the need to _know_ had been compelling. So the idea of having a first experience with some dude willing to do all the work sounded pretty awesome.

He hesitated before pressing the ‘Reply’ button. And he hesitated some more before sending the email he had taken a good half hour to write. His reluctance probably had more to do with the accompanying picture than the message itself. He had never sent a dick pic to a guy before.

Taking a deep breath, Dean sent the email and got up to grab a beer. It was still a bit early but he needed something to calm himself down. Better that than some Jack, he surmised.

The pinging sound from his email software almost made him choke on his beer. It couldn’t be the guy writing back already, could it? Since Dean had been honest about his inexperience, he was probably telling him to get lost.

 

\------------------------------------------------------------

_ Dear Impala67,  _

_Thank you for showing interest in my proposition. Even though I can_  
_appreciate the picture you attached, I have come to realize my request_  
_could have been clearer. If your penis is quite lovely, I was actually_  
_expecting a photo of your face. I understand if you’d rather stay_  
_anonymous for the time being but know that if this is the case, I will_  
_elect to cease all communication._

_ In the hopes of hearing back from you soon.  _

_P.S.: Please find attached a picture of my own erect penis. I can_  
_understand if this type of information is of importance for you. I agree_  
_that a little under seven inches is, indeed, a desirable size. I hope that_  
_my own six and a half inches will be to your liking._

_[ BornWingless@yippee.com ](mailto:BornWingless@yippee.com) _

_ \------------------------------------------------------------ _

 

Dean had to read the message a couple of times, a little put off by its formal tone. He couldn’t yet decide if he found it to be cute or creepy. It occurred to him that he could be talking to a total weirdo. And if that was the case, he hoped the guy would be butt ugly. He’d be much easier to turn down that way.

He scrolled down to find the aforementioned picture. He let out a shaky breath when he saw a nice cock – thicker than his, although smaller – proudly displayed on a backdrop of chiseled hipbones. At the sight, Dean’s mouth watered and his dick perked up. If that wasn’t clue enough…

 

\------------------------------------------------------------

_ Hi BornWingless,  _

_ Sorry for the dick pic and details, man. First time I answer one of these.  
I’m sending a selfie I took just now. I can expect the same from you?  _

_[ Impala67@umail.com ](mailto:Impala67@umail.com) _

\------------------------------------------------------------

 

This time the answer came back even faster.

 

\------------------------------------------------------------

_ Impala67,  _

_ You are very handsome. I may be willing for us to meet if my own  
picture is satisfactory to you as well.  _

_ [ BornWingless@yippee.com ](mailto:BornWingless@yippee.com) _

_ \------------------------------------------------------------ _

 

 

\------------------------------------------------------------

_ BornWingless,  _

_You look pretty good yourself. Before we meet though, can I ask why_  
_you don’t want to reciprocate? I find it weird that you wouldn’t want to_  
_get off._

_[ Impala67@umail.com ](mailto:Impala67@umail.com) _

\------------------------------------------------------------

 

 

\------------------------------------------------------------

_ Impala67,  _

_I didn’t say I didn’t want to, I said I didn’t mind. If offering fellatio is_  
_not something you can do, I won’t demand it. As for bottoming, I have_  
_a very sensitive prostate so I find it quite enjoyable. I know not everyone_  
_appreciates being penetrated. Still, please know I will provide if you_  
_wish that I do._

_ How do you feel about other types of caresses and kissing?  _

_ [ BornWingless@yippee.com ](mailto:BornWingless@yippee.com) _

\------------------------------------------------------------

 

Dean would be lying if he were to say the email exchange wasn’t making him a little hot and bothered. He didn’t even mind the guy’s proper writing style anymore. 

 

\------------------------------------------------------------

_I don’t know if I want to offer it or not. I’m thinking I should at least try,_  
_you know? Might as well get the whole experience. I shouldn’t mind_  
_touching or kissing… I think…_

_ Doesn’t it freak you out that I’m some kind of gay virgin?  _

_[ Impala67@umail.com ](mailto:Impala67@umail.com) _

\------------------------------------------------------------

 

 

\------------------------------------------------------------

_ Impala67,  _

_Virginity is not something that would deter me, would it be gay or_  
_otherwise. If you wish to experiment with me, I will be more than glad_  
_to help. Please know that I will still keep my end of the bargain, even_  
_if you were to change your mind mid-fellatio._

_ [ BornWingless@yippee.com ](mailto:BornWingless@yippee.com) _

\------------------------------------------------------------

 

 

\------------------------------------------------------------

_Sounds good. But I intend on finishing whatever it is I start. ;)_

_So, I don’t know how many guys you got in line but the earlier I know  
if you want to get together, the better._

[ _Impala67@umail.com_ ](mailto:Impala67@umail.com)

\------------------------------------------------------------

 

 

\------------------------------------------------------------

_ Impala67,  _

_I had a couple of responses but didn’t find the following communications_  
_acceptable. Right now, my interest resides in you alone. If you feel the_  
_same, I would love to see you tonight. I have a work related activity_  
_scheduled for this afternoon. Could you meet me at my hotel  around nine?_

_ [ BornWingless@yippee.com ](mailto:BornWingless@yippee.com) _

\------------------------------------------------------------

 

 

\------------------------------------------------------------

_Nine is good for me. Send me your information._

[ _Impala67@umail.com_ ](mailto:Impala67@umail.com)

\------------------------------------------------------------

 

 

\------------------------------------------------------------

_ Impala67,  _

_I will wait for you in the lobby of the Ambassador Hotel, in downtown _  
_Kansas City. Please don’t be late. And if you change your mind, I would_  
_appreciate that you let me know as early as possible. I would have to_  
_make other arrangements._

_ [ BornWingless@yippee.com ](mailto:BornWingless@yippee.com) _

\------------------------------------------------------------

 

 

\------------------------------------------------------------

_No worries, I will. See you later._

[ _Impala67@umail.com_ ](mailto:Impala67@umail.com)

\------------------------------------------------------------

 

As he hit ‘Send’ on his last message, Dean noticed how fast his heart was beating. As if only now realizing what he had just agreed to. Dean Winchester, reputable ladies’ man, had made plans to go meet some guy at his  hotel to  fuck . Even worse, he had been the one to instigate it. To some extent, anyway.

With a trembling hand, he opened a new email window, ready to tell the other man he had changed his mind. He’d understand, right? Anyway, it’s not like they knew each other. They had seen each other’s face, and dick, but nothing more.

He stared at the screen for a while, unable to find anything to write. After a heated internal debate, the part of him that felt horny and adventurous won the battle. He closed the email window and shut down his computer, resolute in keeping the temptation at bay.

Dean glanced at his watch to see it was just about to hit noon and sighed. The day would be a long one.

 

~ • ~

 

At seven thirty, Dean came out of the shower to find his brother sitting in the kitchen. He was eating a slice of the pizza Dean had ordered for dinner.

“Hey, Sammy! Didn’t think I’d be seeing you today,” he said, toweling his hair. “Weren’t you supposed to go to Jessica’s after work?”

“Her roommate has her boyfriend over so Jess will come here instead. You don’t mind, do you?”

Any other day, Dean might not have appreciated the late warning but since he already had plans, he decided to let it slide.

“Nah, it’s okay. I’m going out so you’ll have the place for yourselves.”

Sam gave his brother a bright smile. “Ah yeah? Got a hot date or something?”

“Some kind of date, yeah,” Dean said with a shrug. He wasn’t about to tell his brother where he was going, or why.

“Do I know her?”

“Nah, you don’t. We just met actually.”

“I could still know her. What’s her name?”

Dean groaned as he turned around. “Listen, dude… we can do the twenty questions some other time, all right? I gotta get ready,” he said as he fled to his room.

He knew that if his brother kept pushing, Dean would eventually slip. And using genderless pronouns wasn’t a game he felt like playing. His brother would not judge him, that wasn’t the issue. But he knew Sam would probably want to talk about Dean’s feelings and how he identified himself now. And at this point in time, he wouldn’t know what to answer.

He stayed in his room until it was time to leave, unable to figure out what to wear. Not that he thought they would keep their clothes for very long, but it was the Ambassador  Hotel . You only went there if you had money – lots of it – and not a single person in that place would be wearing jeans and flannel. 

The nicest clothes Dean owned was the suit he wore to his dad’s funeral three years ago. At least the pants made his ass look awesome. He decided to wear them with a simple red button down, rolling up the sleeves up to his elbows. This and his dad’s leather coat should be classy enough for the snotty  hotel ’s clientele.

 

~ • ~ 

 

Dean looked around as he walked in the posh lobby, trying to find his _date_. Most tables were occupied, just not by the guy from the picture. He headed for the bar, thinking the man could be waiting for him somewhere in the shadows. This, or Dean had been played or stood up.

“Impala67?”

A soft tap on the shoulder accompanied the question. He turned around to find the man from the picture. If it was indeed him, Dean had to admit the picture had not done the stranger justice at all. He didn’t just look good, he was gorgeous. 

Glad to see the man be not much shorter than himself, he smiled, admiring the chestnut hair and luminous blue eyes. Dean had to wonder for a second if the guy wore contacts or if the lobby’s lighting was just weird. But whatever it was, he decided he liked it a lot and smiled wider.

“Hi, I’m Dean,” he said, remembering they hadn’t exchanged names. He wasn’t about to call the man by his email address.

“Hello, Dean. I’m Castiel,” the other man said as they shook hands, in a deep and raspy voice. 

Not picking up on Dean’s enraptured expression, Castiel turned to lead the way towards the elevators. Dean followed without a word, as if under a spell.

They both kept silent the whole way up, Castiel relaxing only when the door closed behind them. Dean didn’t really see that as he was gobsmacked by what looked more like a suite than a room. There was a kitchenette with a dining area and a living room. There even was a staircase leading to a second level.

“Man, you must be loaded,” he said as he entered the elegant space.

“Does that make you uncomfortable? Would you prefer– ”

“What? No, dude, I don’t care. It’s just… I’ve never been in a place like this, is all,” Dean assured Castiel as he looked around. “And just so you know, I’m no thief so… don’t worry, all right?”

“I didn’t think you were,” Castiel responded as he opened a wooden cabinet. “Would you like something to drink?”

“Yeah, that’d be good. You got any whiskey?”

The other man nodded, taking out a bottle of Johnnie Walker. “Ice?” he asked, which Dean refused, then poured each of them a glass. He motioned for Dean to join him on the leather sofa.

“Cheers,” he said as he clinked their glasses together.

“Cheers,” Dean replied before downing half his glass in one gulp.

While Dean made a point of not looking at his host, he could feel the blue eyes roaming all over his body. He shuddered, still unsure if he liked the attention or not. He drank the last of his glass before deciding the time had come to break the silence.

“So, how d’you wanna do this? D’you even have a bed in here?”

“Upstairs, on the mezzanine. I know this is your first experience so I wouldn’t want to rush you into it,” Castiel answered before taking a much smaller sip of his own drink. He put his glass down and grabbed the bottle to pour Dean some more whiskey.

Dean nodded his thanks and took another sip, a smaller one this time. “Yeah, don’t worry about me, man. I’m good,” he had time to say before Cas grabbed Dean’s glass to put it on the coffee table.

“If you don’t like what I’m doing, just tell me,” he murmured as he leaned into the younger man’s space. Dean swallowed as Castiel’s face got close to his and when their lips met, he jerked himself back.

The blue eyes shone with mirth. “All right, no kissing,” Castiel said, putting a calming hand on Dean’s thigh.

“No… it’s okay… I mean… sorry,” Dean tried to explain, contrite. “Let’s try again, all right?”

Cas gave a soft nod but didn’t lean in for a kiss. Instead, he touched Dean’s face, brushing his thumb over his bottom lip. “Close your eyes,” he said. 

Dean obeyed, trying to concentrate on anything but his galloping heart. He took a deep breath, only to be overcome by Castiel’s smell. And hell if it wasn’t one of the nicest things to ever have tickled his nostrils.

Bathing in the sensual mix of peppercorn, grapefruit, and cilantro, Dean didn’t flinch when Castiel’s mouth landed on his again. He accepted the gift, unmoving, letting him lick and nip at his lips. It felt like a long time, but it really only took a second for Dean’s brain to get with the program. Before he knew it, he had both hands crowding the man’s face and was kissing him back, all shyness forgotten.

Hungry, he took control of the embrace, letting out a small groan as his tongue was granted access. He found himself delighted by the bursts of whiskey and cinnamon he could taste on the other man’s tongue. Every inch of his skin tingled as though his veins had been filled with champagne.

“That was… nice,” Dean whispered when they separated, in dire need of fresh oxygen. 

Castiel nodded in assent, keeping his eyes closed. With a satisfied humm, he moved forward to straddle the younger man’s lap. “Is this all right?” he asked before leaning in to give sloppy kisses on Dean’s neck.

Sparks ignited throughout his whole body. “Huh huh…” he confirmed, letting his head fall backwards to give Castiel a better access. He grabbed at the man’s hips to try and stay grounded.

“I think we should take your clothes off,” Castiel said as he started unbuttoning Dean’s shirt. 

It was slow and sensual, something Dean wasn’t used to. Not with his one night stands anyway. He squirmed under the attention, hoping the other man would understand he should pick it up.

He understood. “Are you in a hurry? Do you have a wife you need to go back to?”

Dean huffed, wondering if he should be insulted. But of course, the way they had met was certainly enough to warrant such questioning.

“Nah, man… I guess I’m just impatient,” he said with honesty, surprising even himself.

Castiel stopped kissing him, looking up to lock their eyes together. “Let me make this good for you, all right? Let yourself be taken care of… somehow I doubt it happens often.”

If Castiel saw the surprise Dean’s eyes, he didn’t comment on it. Instead, he went back to undoing his shirt, kissing his way down. Dean was grateful for that, not in the mood to start dwelling on the suckage that was his life. Or on how the guy could have even picked up on it.

All non-sexy thoughts flew out the window the second Castiel’s tongue landed on his nipple. That right there was one of Dean’s most sensitive spots, making him buck his hips up. With a delighted growl, Castiel sucked and nipped at the hardening nub as he pinched the other one between his fingers.

“Fuck… Cas…” Dean hissed. “I mean Castiel,” he corrected himself.

“Cas is fine,” Castiel replied as he pushed the red shirt off of Dean’s shoulders. “You are so beautiful,” he said under his breath before mouthing at the younger man’s newly uncovered skin. “Those freckles…”

Whatever Castiel had said before, it didn’t make Dean less impatient. He needed to feel skin under his fingers, craving the heat. But the full suit and tie the man still wore didn’t make things easy. Without asking, Dean took off Castiel’s suit jacket, then tried to get rid of his stupid blue tie. Stupid only because it was yet another thing standing in his way.

Feverish, Dean abdicated, instead choosing to pull Castiel’s shirt out of his pants. He let out a relieved breath when he felt the warm skin under his hands. _“That’s the stuff,”_ he thought as they started kissing again. Castiel squirmed a little on his lap, Dean’s mind starting to spin when he felt their erections brush together.

“Aaaah, shit,” he moaned in Castiel’s mouth, circling his arms around the older man’s waist. “You’re so hot,” Dean said again as he kissed up the jawline to suck on his earlobe.

“Ears don’t do much for… aaaah,” Castiel tried to warn but Dean had noticed. He was now licking down his neck to suck a bruise just below his adam’s apple. “Don’t… don’t mark me… not there… please…” Castiel asked between ragged breaths.

“Take off your shirt,” Dean replied as he let him go. He could have done it himself but he feared he’d end up tearing it apart. Not that it wouldn’t be hot if he did.

“Want to go upstairs?” Castiel asked, taking his shirt off much quicker than he had done Dean.

Dean nodded, letting go of him. For half a second, he had wanted to climb the stairs with Castiel still straddling him. That’s what he would have done if he had been with a girl. But Cas was almost as tall and not so much lighter than he was. Trying to carry him up the stairs wasn’t something he felt should be tackled at this very moment.

Except that they might have gotten to the bed a lot faster. Instead of the minute it should have taken, it took close to ten, with about five spent making out about half-way. It should have been uncomfortable for Cas who had been lying down with the steps’ edges digging into his back. But he didn’t seem to care, his arms and legs tight around Dean.

When they  finally reached the bed, they had somehow lost their pants. They lied on the bed in their underwear, kissing and roaming their hands all over each other. This was probably one of the most sensual encounter Dean had ever had and, to his own surprise, he couldn’t find anything wrong with that.

“How did you prepare?” Castiel asked after a while, his breath warm on Dean’s lips.

“What do you mean?” Dean responded, chasing the other man’s lips down.

As sole answer, Castiel snaked a hand in Dean’s underwear, a finger or two gliding down the cleft of his ass. Dean’s breath hitched and his hips gave a little jerk. Assplay wasn’t something new for him, he had explored a little, either by himself or with some adventurous ladies. But the context was now different and, quite frankly, a bit scarier.

Castiel let his mouth go. “You seem uncomfortable. I will not go near your anus then.”

Even though Dean was indeed uncomfortable, he couldn’t not laugh at Castiel’s words. “Dude, I didn’t wanna say anything about the way you speak but… just don’t say anus, all right?” 

His request granted him with a quizzical look. “I am told to be a little too proper at times, yes. Sorry if I offended you.”

Dean smiled. “I’m not offended, it’s just… it’s weird is all. And yeah, I washed my ass if that’s what you wanted to know. I’ve… I’ve experimented before…”

“What does it mean for you? Can I touch you there?” Castiel sent the younger man a fiery gaze. “Could I kiss you there?” he asked again as he got on all fours, cradling Dean’s body under his. 

Breathing heavy, Dean could only nod, his eyes dark with desire. Castiel leaned forward and started kissing his chest, leaving a trail of wet skin as he traveled down towards his navel. He stopped there for a second, dipping his tongue in before continuing down. Once more, Dean felt impatience bubble up as he felt Cas kiss along the waistband of his underwear.

“For  fuck ’s sake, Cas… do something,” he said in a growl, glancing down to see the man smirking at him. 

“I’m doing something,” he replied, sliding a finger where his lips had just been. “You are quite impatient. If you’re so anxious, why don’t _you_ take control?” At Dean’s wrecked whine, Castiel’s eyes darkened. “That’s what I thought,” he declared before mouthing at Dean’s erection through the cloth.

“Aaaah… jesus… shit,” Dean gasped, carding a hand in Castiel’s hair.

“You have such a dirty mouth, Dean,” Castiel said as he teased him, grazing his fingers over the head peaking at the waistband. “I do love a dirty mouth. Tell me what you want, Dean.”

“I want your mouth on my junk. I wanna come down your throat. That’s what I– oh shit, yeah… like that,” Dean cried when his whole length got engulfed in Castiel’s mouth. “Ooooh… shit… I wanna  fuck …  fuck your face.”

But Castiel seemed to have other ideas as he held the younger man’s hips down, not letting him buck up. Dean’s frustration was short lived as Cas swallowed and hummed around him. This with the tongue twirling were bringing him close to the edge at the speed of light.

“Ca… Cas… stop… too fast…” he said in a scratchy voice, his hand clenched in Castiel’s hair.

Castiel let Dean slide out, making him whine as he gave the slit a light flick of his tongue. “What do you wish I do now?” Castiel asked, stroking Dean’s leg softly. “Want to turn over? Want me to perform anilingus on you?”

Dean laughed again. “Dammit, Cas. Eat out, all right? That’s the term… or rimming. Not ani-whatever-you-said.”

“You still understood what I meant.”

“Yeah, I did… but it’s not sexy. But no, that’s not what I want,” Dean said again, pushing himself into a sitting position. He licked his lips, his eyes drawn to the tent in Castiel’s own underwear. “I wanna do you now. Blow you, I mean,” he added, unable to look away.

“I’d like that,” Castiel said, lying down on the bed where Dean had been before. The covers were warm on his back. He exhaled loudly and closed his eyes when Dean pulled down his underwear. It didn’t take long for strong fingers to close on his semi-erect length.

Dean gave a couple of tugs, taking the time to experiment having someone else’s dick in his hand. It was weird, foreign, but far from unpleasant. He loved feeling the hot flesh grow under his palm. It only felt natural to wrap his lips around the head and tease it with his tongue.

“Aaah,” Castiel let out under his breath. Finding it encouraging, Dean sunk lower, until the head hit the back of his throat, making his gag reflex act up and his eyes water. With a disgraceful noise, he took his mouth off Castiel.

“Sorry,” he mumbled, a little embarrassed. He kept pumping Castiel’s dick as he took a second to breathe.

Castiel brought a soft hand to Dean’s face. “You’re doing great.”

Delighted by the praise, Dean licked his lips and sank down on Castiel’s dick again. He quickly found a good rhythm, bobbing his head and using his fist on what he couldn’t fit in his mouth. Still, he felt it wasn’t enough, thinking back to some stuff that had been done to him over the years.

He let go of Castiel with a wet pop, smirking when the man let out a low whine. He didn’t make him wait, dipping lower between his legs to lick and suck at his balls, still with his fist working the shaft.

“More… I need more,” Dean heard Castiel croak as he flattened his feet on the bed and spread his legs. 

At this moment, any doubt Dean could still have had evaporated; he was so damn bi. With a hungry moan, he shoved a thumb in mouth. He spreaded Castiel’s ass cheeks with his other hand. His wet thumb easily slid to the first knuckle, the man’s hole already loose and wet.

“More…” Castiel whined again, making the whole thumb disappeared inside him as he bucked down.

“Damn, Cas… you’re so hot,” Dean said, softly pumping his thumb in and out. Without a second thought, he took his hand out of the way to replace it with his mouth. 

“Shit,” he heard Castiel say in a hiss. Not even a second later, a bottle of lube and a condom were thrusted in his hand. “I can’t wait anymore,” Castiel said in a pleading voice. From where he was, Dean couldn’t see much of that electric blue, the pupils blown too wide. “On your back,” Castiel ordered, panting.

Dean obeyed, once more getting on his back. He was hard enough but still tugged a couple of times on his dick before rolling the condom down. Castiel had already grabbed the lube and squirted some in his hand. He took a second to warm the gel before spreading a generous coat over the condom.

Enthralled, Dean watched Castiel as he shoved a couple of his lubed fingers in his hole. He was tempted to ask him to turn around so he could see better but didn’t. He was much more looking forward to the man sinking down on him than seeing him play with his ass.

Finally ready, Cas hobbled forward with his knees on either side of Dean. He grabbed Dean’s dick at the base, aligning himself. For an instant, it felt like time stopped, starting back again when the head softly passed the rim and both men exhaled in unison.

“Fuck… that feels… awesome…” Dean muttered as Castiel slowly bottomed out.

Once fully sheathed, Castiel grounded himself with both hands on Dean’s chest, trying to regulate his breathing. When he slid up and sank back down in a faster motion, Dean couldn’t hold a surprised moan. He’d never been inside anything so tight and hot before. Overwhelmed, he grabbed Castiel by the neck to pull him down for a kiss.

Castiel didn’t stay down for long, pushing himself back to hold onto Dean’s legs and pump his hips. After a couple of minutes, he let Dean slide out, making them both wince. Before Dean could say anything, Castiel coated him with some more lube and turned around to straddle him again.

“Reverse cowgirl?”

“Reverse cowboy,” Castiel corrected in a broken voice as he sank back down on Dean, much quicker than the first time. After moving around a bit, he let out a loud moan. “Dear god,” he breathed, now bouncing up and down in a fast pace, moaning at almost every thrust.

Knowing he wouldn’t last much longer, Dean squirted some lube in his hands. He sat up, holding on to Castiel’s waist. With his other hand, he grabbed Castiel’s dick, doing his best to jerk him off in a similar rhythm.

Dean came first, his groans muffled by Castiel’s back. It must have been all the other man needed because he came not long after, his insides clenching on Dean’s over sensitive dick. They rode the wave together, holding on to one another, wheezing.

Drained, Dean let his body fall back on the mattress. He had wanted to pull Castiel down with him but he had resisted. Instead, he slowly got up, letting Dean’s dick slide out. He pulled the condom off and disappeared behind a frosted glass door. After a couple of minutes, he came back to bed with a warm washcloth for Dean.

After taking care of his young lover, Castiel lied back on the bed, facing him. Dean noticed the space between them and gave him a confused look.

“You’re in the damp spot. You may want to come closer to me.”

Dean smiled and did as suggested, letting the other man turn him around and pull him into his own body. They spooned, with Dean as the little spoon, a position he had never been in before. Against all odds, it felt natural enough for him to fall asleep.

 

~ • ~

 

When Dean opened his eyes again, it was to a soft hand stroking his dick. He couldn’t have said how much time had gone by but it seemed enough for him to already be getting hard. He turned his head, his mouth searching for Castiel’s own. As they found each other, Dean felt Castiel’s other hand caress his jaw, pushing them together.

He grabbed the leg Cas had draped over him, desire overcoming him once more. His mind racing, Dean wondered what would be happening now. Cas had said he loved to bottom and if the surprise stroking of his dick was anything to go by, it seemed like he wanted to ride him again. But Dean wasn’t sure that’s what he wanted.

He rolled around to face Castiel who opened his eyes, if only for a second. Grabbing Dean’s face, he crashed their mouths together. Dean let him explore his mouth for a while, images of himself sinking down on Cas dancing inside his eyelids.

“Cas, I want it,” Dean blurted in a low voice when they separated.

“Say it like you mean it, Dean,” Cas ordered before starting to nip at his jaw.

Dean cleared his throat, swallowed, exhaled. 

“Cas, please plow my ass,” he said, his tone falsely innocent.

Castiel laughed. “Your wish is my command.”

It was Dean’s turn to laugh. “I kinda noticed it’s been the other way around so far.”

“I guess we are versatile, then.”

“Still not sure how versatile I really am,” Dean felt the need to precise.

“Let’s find out, shall we?”

Dean had always known he was on the submissive end of the spectrum. He loved assertive women and got off on letting them manhandle him in bed. Turned out it wasn’t so much different when it came to guys. He let Castiel move his body around until he was on his knees with his ass sticking out in the air.

“Your an– hmm… your hole is very pretty. So tight, and so pink,” Castiel praised as he spread Dean’s ass cheeks. He gave the sensitive skin a soft kiss, making Dean shudder. “I would love to open you up. Would you let me do that?” he said again, taunting the rim with the tip of his tongue.

“Sh… shit… yeah… please… hunh…”

Castiel kept licking and kissing his hole for a little while, delighted by each of Dean’s noises. “You’re so responsive, Dean. So sensitive. You think I can make you scream?” he asked as he grabbed the lube. Not waiting for an answer, he massaged the rim with a lubed up finger.

Dean sent his hips backwards. “Fuck, Cas… You’re killing me here…”

“Patience, Dean. You don’t want to rush this.”

With a groan, Dean let his head fall on the pillow between his forearms. He was already hard and leaking, even though close to nothing had happened yet. All the experimentation in the world could not have prepared him for how good this felt.

When Castiel’s finger breached him, Dean let out a shrill mewl and couldn’t find it in himself to care. He had a stranger’s finger in his ass and it was one of the best things he had ever felt. The sharp pain subsided quickly, thanks to Castiel’s tender ministrations. As he moved his finger in a delicate back and forth motion, he had his other hand caressing the small of Dean’s back, soothing him.

Dean let out a shaky breath when Castiel took his hands off him, but it didn’t last long. The hand soon returned to rest on Dean’s back as two wet fingers were pushed in his ass. Like before, Dean hissed from the pain but this time it lasted even less longer. Soon enough, the fingers were coming in and out at a moderate pace, all pain forgotten.

Cas had found the bundle of nerves and kept stroking it, leaving Dean just about to come. He grabbed the base of his dick, intended on saving some room for the main course.

“Cas, man… just  fuck me already,” he barked in the pillow. “I’m so close…”

“You’re not ready.”

The fingers left him empty once more. “Cas…” he whined when they came back in, this time with a third one tagging along.

Opening Dean up rather than teasing him now, Castiel leaned forward to kiss the back of his neck. “Soon,” he promised under his breath. A couple of thrusts later, he sat back on his knees. He rolled a condom over his length and coated it in a generous amount of lube.

“Now, you tell me if I hurt you,” he said, only to be answered with a sharp nod and a groan. He held onto Dean’s hip, aligning the head with his other hand. “Breathe, Dean,” he said as he tried to push in, his thumb stroking soothing circles on the skin.

“Aaaah… hunh… shit!” Dean peaked over his shoulder when he felt the head slide in. Castiel’s eyes were closed and his brows furrowed, looking deep in concentration. “Look at me,” he asked, needing to feel something else than the sharp pinch in his ass. When the darkened pupils met his, it felt like a stab in his heart. 

“Move,” he said in a low growl, not letting his stare falter. As Castiel sank further inside him, Dean felt the heat shoot up his spine, setting his whole body on fire. 

“You aren’t as submissive with someone penetrating you, Dean. I like it a lot,” Castiel said as he amped up his speed.

Dean turned back around to bury his face in the pillow. “Shut up.”

Even if he had wanted to, Castiel would not have been able to say another word. All that came out of his mouth were ragged breaths and throaty moans as their bodies smashed together. Dean wasn’t in a better disposition, panting and moaning just as much, basking in the sensations of his prostate being stimulated and Cas’ balls slamming onto his ass.

He couldn’t hold himself anymore and he let the base of his dick go to start stroking the shaft. “I’m… Come with me…  Fuck , I’m so close,” Dean managed to say before sinking his teeth in the meat of his own forearm.

Another couple of erratic thrusts later and Castiel stilled, emptying himself in the condom. Dean came almost immediately, delighted by the pulsing of Castiel’s dick inside him. “Cas…” he cried in a raspy voice as his dick ejected strips of white on the sheets. “Shit,” he said again, unable to find the will to move.

Castiel took the lead once more, sliding out of Dean’s body and helping him lie down. “You are amazing. You did so good, Dean.”

The younger man hummed and nodded, having trouble keeping his eyes open. “Thanks,” he still mumbled, half asleep.

Without answering, Castiel curled his body around Dean’s and held him as he too dozed off, lost in delicious scents of spices, leather, and sex.

 

~ • ~

  

~ • ~

 

It was Dean who woke up first this time, the rising sun sending shades of gold into the room. A little panicked to have spent the night, he sat up, not minding the other man’s arms around his waist. He got up to grab his pants and underwear before disappearing in the bathroom.

He came out half-dressed after taking a quick shower to find Castiel awake, sitting with his back against the headboard.

“Good morning,” he said with a soft smile, giving Dean an appreciative once over.

“Mornin’… don’t worry, I’ll be out of your hair in a minute. I just had to wash a bit, I seriously reeked.” Dean usually wasn’t one to babble, but he couldn’t help himself. He had broken the number one rule of hook-ups and had stayed the night.

“I’m not kicking you out, Dean. I’m actually glad that you’re still here. I was thinking we could have breakfast together.”

Even though he was indeed hungry, Dean didn’t think it’d be a good idea. “Huh… thanks, but… I got my brother waiting for me at home. He must be wondering where I’m at.”

“He didn’t know you’d be here?” Castiel asked.

“Nah… wasn’t ready to have _that_ conversation, you know?”

Castiel nodded, a grave expression on his face. “Did anybody know where you were?” he asked again. He shook his head when Dean’s contrite expression answered for him. “You should have told someone, Dean. What if I had been a violent individual?”

Dean smiled, starting to relax a bit. “Don’t you worry, Cas. I can hold my own.”

“I don’t doubt that you can but I would urge you not to do this again. Next time you go and meet a stranger, you should tell someone.”

“How about you? Did _you_ tell anyone?”

It was Castiel’s turn to smile. He didn’t answer right away, instead getting out of bed to walk up to Dean. “I did tell my brother, yes. I even texted him just now to let him know I was still alive.” In a soft gesture, he kissed Dean on the cheek, his knuckles grazing the stubble on the other one. “I’m going to take a shower now. I would love if you were still here when I came out.”

“Look, Cas… this was fun and all but– ”

“I’m not asking for your hand in marriage, Dean. But I understand if you would rather leave. Please know that I really appreciated our night together.”

Without waiting for an answer, gave a chaste kiss to Dean’s lips before disappearing in the bathroom.

If Dean were to be honest, he knew he wanted to stay a while longer. This may have been a one night stand, it still felt like a little more than that. As he walked down the stairs, he wondered what it was that made this encounter different from all the others. Apart from it being with a guy and getting his ass broken in, of course.

He went to the dining table where his leather coat had been thrown and grabbed the phone from his pocket. There hadn’t been a single incoming call or text. He thumbed down to find his brother’s number. It took several rings for Sam’s sleepy voice to be heard.

“Wha’?”

“Hey Sammy… just wanted to tell you I’m not dead and stuff.”

“Hmm… fine… see ya.”

“Listen… I’ll be over later, okay? I might stay a little longer.”

“Good for you. Can I go back to sleep now?”

“Yeah, yeah… see you la– ”

But Sam had already hung up, making Dean smile. His brother usually was quite the early bird, he must have had a late night as well. Apparently, it had been a very fruitful night for both Winchester boys.

With Castiel still in the shower, Dean rummaged in the cupboards to find coffee. He’d been to enough cheap hotels in his life to know that the provided coffee was always on this side of awful. But in this place, there was no way it would be bad. He surprised himself to be disappointed not to find an espresso machine but rather an ordinary percolator.

“I’m glad that you decided to stay, Dean,” he heard Castiel say. He turned to watch him as he came down the stairs, wearing the  hotel ’s complimentary bathrobe.

“Yeah… I thought breakfast could be a good idea.”

“You called your brother, I assume?”

Once more, Castiel appeared to be reading Dean’s mind but he didn’t dwell on it. So what if the man was more perceptive than most? It’s not like they would see each other again after that day anyway.

“Yeah. He didn’t appreciate it so much though.”

“It _is_ quite early,” Castiel confirmed as he glanced at the digital clock on the microwave. He opened a drawer and took out the  hotel ’s menu. “Are you in the mood for something specific?”

As he poured two cups of the dark brew, Dean shrugged. “Dunno… you take milk or sugar in your coffee?” he asked as he brought the mugs to the table.

“No, black is good, thank you.”

Dean smiled, liking his coffee in the same manner. He brought his chair closer to Castiel’s, ready to argue that it’d be easier for them to look at the menu together. But Cas didn’t say a word about it.

“In the mood for sweet or salty?” he asked as they both read.

“I’m so hungry, not even sure what I want. Can we get both?”

“We could take whatever savory breakfast we want and order an extra serving of pancakes. Would that work for you?”

“I guess. I’m surprised the prices are so low though. I would have thought this place would charge you ten bucks for a single piece of toast.”

It made Castiel laugh. “Don’t worry about the prices, Dean. It’s all taken care of.”

Even though he knew the older man hadn’t meant it like that, Dean still felt attacked in his pride. “Look, man… I don’t care that you’re rich, I can still pay for my own food.” 

Before he could get up and leave, Castiel’s soft hand landed on his. “Of course, Dean, I know that. I should have precised that I’m not as rich as you may think.” At Dean’s suspicious scowl, he continued. “I’m here on business, even _I_ am not paying for this room.”

“Won’t your boss give you shit for having guests?”

“That would be my editors, not my boss. And no, they don’t mind.” Castiel smiled as he let Dean’s hand go. “My brother is my agent, so believe me when I say that he made sure to deal us nice  hotel accommodations. I am here on a book signing tour and– ”

“Man, you’re famous? Maybe I read your stuff?”

“Moderately famous, if I may say so myself,” Castiel answered with a crooked smile, “but I doubt you would have read any of my work. Unless you are into history, religion, or philosophy.”

At Dean’s grimace, Castiel erupted in laughter. “That’s what I thought. It is a very tight niche.”

“You can make money writing shit like that?”

“When I say I am moderately popular, I should have precised that I may be at the top of my field. Moderate only because of the small number of potential readers. Some of my most popular works are now part of several universities’ curriculums.” 

The same words coming from anybody else, even from Dean himself, could have sounded highly conceited. But something in his tone and manners made it seem like nothing more than random information. As if to confirm Dean’s impression, Castiel didn’t say another word about his achievements and went right back to their initial topic.

“I will be having the vegetable frittata. How about you?”

“A cheese and bacon omelet sounds good.”

“Excellent. What do you think about pecans for the pancakes?”

“It’s my favorite pie, so pecan pancakes can’t be all bad.”

“I had them earlier this week, they are most excellent,” Castiel confirmed as he went to take the handset next to the sofa. 

After ordering, he came back to the table to sit next to Dean. They kept silent as they drank their coffees, but it wasn’t uncomfortable. Not like it had been the night before. It even was comfortable enough for Dean to feel a little frisky and start playing footsies. Castiel didn’t comment but didn’t move away either, instead spreading his knees a bit. Both men smiled as Dean’s foot made its way upward. 

“Would you like a foot massage?” Castiel asked. 

Dean shook his head as he snaked his foot between Castiel’s thighs. He smiled wider when he felt no fabric standing in the way. “You dog,” he commented as he softly wiggled his toes on his naked crotch.

The smile on Castiel’s face had some ravenous undertones as he leaned forward over the table. “You know what I haven’t done?” he asked in a low voice, licking his lips. Dean shook his head, mesmerized. “I haven’t performed fellatio on you.”

“Yeah, you did…” Dean countered, not that he intended on refusing.

“Not to completion.” Castiel rose from his chair and grabbed Dean’s hand to pull him towards the living room portion of the suite. He sat on the sofa, making Dean stand in front of him. “Fuck my face,” he said lowly as he worked the pants open, agreeing to Dean’s request from the night before. “I want to drink you down,” he said again before wrapping his lips over the head.

Sensing Dean’s hesitation, Castiel grabbed him at the hips and pulled him forward until his nose brushed the nicely trimmed pubic hair. He hummed as he pushed him back and pulled him forward again. Dean stopped fidgeting and took control, both his hands clutched in the already messed up brown hair.

Castiel kept his hands on Dean’s hips, not lessening his grip but not steering him anymore. He sucked and swallowed around Dean, his tongue warm on his shaft. This time, when Cas’ fingers migrated towards his hole, Dean didn’t flinch. He welcomed the soft touch, memories from last night shooting electricity all over his skin.

Dizzy with lust, he grabbed one of Castiel’s hands to suck on his fingers. “In me,” he groaned, working his hips back and forth. 

The sting from the previous activities was present but dull. The finger Cas pushed inside his hole felt like it belonged there, filling a void Dean hadn’t known was there. He came less than a minute later with his dick deep in Castiel’s throat and a finger pumping his ass.

“Shit…” he let out in a shaky breath.

With his mouth still on Dean, Castiel was also bringing himself to the edge at a furious pace.

“Cas, let me–” Dean started only to lean forward when Castiel moaned around him as he came from his own hand. “Fuck… get off… too much…” he managed to say as he tried not to fall to his knees.

Looking up at Dean, Castiel obeyed, letting him go with a soft pop. “That was lovely,” he purred as he fell backwards on the sofa. 

With a pleased smile, Dean sat beside him and grabbed the hand Castiel was about to wipe on his bathrobe. Gazing into his eyes, he brought it to his mouth. He had only ever tasted himself and felt the need to taste another man.

“Hmm… yours is better than mine,” he said, surprised by the faint hint of sweetness on his tongue.

A knock at the door prevented Castiel from commenting. He got up, wiping his hand on his bathrobe and adjusting it as he went to answer. A young man came in, pushing a cart towards the dining table. While he transferred their breakfast, Cas ran back upstairs to grab some money from his wallet.

Still in a daze, Dean gave the young man a polite smile. The employee replied in kind as he pushed the cart aside, his smile getting wider as his eyes landed on Dean’s crotch. Only then did Dean realize his pants were still undone and his flaccid dick was hanging out.

“Shit,” he blurted, heat blossoming on his face as he refastened himself. He heard Castiel clear his throat as he came back downstairs. There was no way he hadn’t witnessed this. Dean stayed on the sofa, looking out the tall windows, until he heard the door close.

“He’s gone now, come have breakfast,” Castiel said.

As Dean came to sit with him, Castiel couldn’t hold it any longer and erupted in laughter. And yeah, it was pretty funny, Dean decided. Soon, both were laughing so hard tears were streaming down their faces.

“I think the bellboy appreciated the display, in case you were worried,” Castiel said after being able to calm down a bit.

Dean gave him a wide grin. “Of course he did. It’s a very nice cock.”

Castiel nodded, smiling just as much. They had eaten about half of their breakfast when Cas spoke again. “Tell me, Dean… I know this was meant to be a one time thing, for either of us. But I was wondering if I could see you again if I come back to Kansas City.”

Wondering if he should have seen this coming or not, Dean took a second to think about it. His first instinct had been to say no but he found that he couldn’t. It’s not like the guy would be spending his time hanging around here now, would it?

“Maybe I was being too forward, it’s okay if–”

“No… I mean… yeah. If you’re ever back here, just call me or whatever,” Dean cut him off, afraid to see him change his mind.

A relieved smile appeared on Castiel’s lips. “I intended on sending you emails but if you prefer that we exchange numbers, I wouldn’t be against it.”

“Yeah, it’s easier I guess.” Dean grabbed a pancake to put it on his plate and doused it in syrup. “So, wher’you from?” he asked around his first bite.

“I was born in Pontiac, Illinois. I moved to New York for college and never came back. How about you? Are you a Kansas City native?”

“Nope. My brother and I, we were born in Lawrence, it’s about an hour from here. But then my mom died and my dad moved us around a bit. I came here with Sam five years ago when he got into college.”

Castiel nodded as he too grabbed a pancake. They kept eating their breakfast, silent again. Dean had been worried at first that they’d be doing the awkward morning after ’let’s get to know one another’ thing. Apparently, neither of them were in the mood for that.

Even though Dean had been ready to leave as soon as he woke up, it was Castiel that put an end to their date shortly after all the food was consumed.

“I would love to spend some more time with you, Dean, but I have a book signing in about two hour. My brother will be here to get me soon. I’m afraid this is where we must part ways.” He grabbed Dean’s hand. “I’m really glad to have met you. And I honestly hope that we can meet again someday.”

Dean’s heart quickened, half panic and half elation. “Yeah, me too, Cas. I couldn’t have hoped for a better first time.”

“I take this is the beginning of a new life for you?”

“Dunno… Not sure it’s gonna change that much, you know? I’m the same guy I was yesterday. A little more experienced, maybe,” he said as he got up. He looked around to find his shirt bunched up in a corner of the sofa. He put it on, followed by his leather jacket.

After they exchanged phone numbers, Dean walked to the door, pulling Castiel behind him. He couldn’t imagine leaving without getting one last taste of the man. They ended up kissing for longer than they should have, forced back to reality when a playful knock was heard on the door.

“Damn… Gabriel,” Castiel murmured against Dean’s lips, making him laugh.

“You’re gonna be late,” Dean said before kissing him once more.

A second series of knocks startled them again. “I have to answer, he knows I’m here.”

“Cassie! On the count of three, I’m using my own key,” they heard Castiel’s brother warn from the other side of the door. “Tell your boy toy to– oh, hey, Cassie.”

In the hall stood a blond man, shorter than the both of them. His face held a devious grin as his gaze traveled between his brother and the tall green-eyed stranger. “And what a boy toy he is,” he commented as he let himself inside the room.

“Dean, this is my brother, Gabriel. Gabriel, this is Dean… he was just leaving,” Castiel said as he pushed the younger man through the threshold.

“Nice to meet you, Gabe,” Dean said as Castiel followed him outside, closing the door just enough so they’d be out of Gabriel’s sight.

“I’m sorry to have to do this, I really– ”

“Don’t worry about it. You remember I was ready to bolt as soon as the sun got up, right?”

With a laugh, Castiel put a hand behind Dean’s neck, pulling him in for another kiss. “I really hope we’ll get to see each other again, Dean. But you’d better leave or I won’t be able to let you go.”

“Until next time, Cas.” Dean gave him one last kiss and walked towards the elevators. 

As he waited, he turned to see Castiel still standing in the hall, looking at him. Before going through the sliding doors, he waved him goodbye, to which Castiel responded with a similar wiggle of fingers. As he descended to the lobby, Dean chuckled, knowing he’d just acted like the biggest dork. But for once in his life, he couldn’t care less.

 

~ • ~

 

When Dean opened the door to his apartment, it was to see Sam and his girlfriend sitting at the table, eating frozen waffles splattered with Nutella. The contrast with his own awesome breakfast – and entire night – made him smile, thinking he could get used to the luxury.

“Seems like someone had a nice date last night,” Jessica said, patting the chair next to hers. “I want to know _everything_.”

Laughing, Dean sat next to the blonde woman. “There’s nothing to say, really. We had some fun, then some breakfast, and now I’m here. The end.”

“So, what now? Will you see her again?”

Dean’s stomach dropped. Of course, he could just say no and it wouldn’t exactly be lying. Except that it would be, seeing as he kind of hoped he’d get to see Cas again someday. And it wasn’t like it was a bad thing to be bisexual, was it?

He looked at his brother. The delighted look on his face was enough for Dean to make his mind. Even though it had been Jessica that had asked the question, he kept his attention on Sam.

“Yeah, about that… huh… I wasn’t with a girl last night.” Obviously, it wasn’t clear enough for Sam who just seemed confused by his brother’s announcement. But Jessica certainly wasn’t.

“No shit! For real? What’s his name?”

“Honey, that’s not what he means. Where were you if– ” Sam interrupted himself when he saw Dean be slightly flustered. He _never_ was flustered. “You were with a guy?” he asked, incredulous.

“Yeah… I… I’m bi, Sammy… I just wasn’t sure before, you know?”

“I’m so proud of you,” Jessica purred as she got up to hug Dean. “So, you’re gonna see him again?” she asked after sitting back down.

Before he could answer, he got engulfed in his brother’s humongous arms. “I love you, man. I’m proud of you too, all right?” Sam said, rocking their bodies sideways.

Embarrassed, but still happy, Dean cleared his throat before wiggling out of the embrace. “Yeah, that’s cool, man. Get off me,” he said, his voice gruff but still with warm undertones. He turned to Jessica to answer her question. “I don’t know if I’ll see him again, he’s not from around here. If he ever comes back, we just might hook up again.”

“What does he look like? What’s his name? Sam, get your brother some coffee, and some for me too. Do you think you could you fall in love with him?”

Dean loved Jessica, he really did. But at that very moment, she annoyed the hell out of him. She was way too giddy and had too many questions. Questions he had hoped he wouldn’t have to ask himself. As Sam placed a cup of coffee in front of him, Dean exhaled, defeated. Not that he would admit it to anyone but he kind of wanted to talk about Cas.

“All right… only because it’s you,” he warned the young woman who squealed in delight. “So, well… he’s got brown hair and blue eyes. It’s kinda weird actually, they’re really shiny, but it’s also hot, you know?” Jessica nodded, urging him to continue. “He’s almost as tall as me, similar built. He’s real cute too.”

“Aw, he sounds adorable.”

Dean smiled at the words. Yeah, Cas really was adorable.

“So what now, the guy’s gone but you’ll keep contact, right?” Sam asked.

“He’s not my boyfriend, Sammy. We had a nice time, is all. Cas lives in New York, it’s not exactly next door, you know?”

“But if he lived around here, would you guys pursue this?”

That was one of the questions Dean had hoped he wouldn’t have to ask himself. Having to answer it now made his hands a little clammy and his heart speed up. ‘ _To hell with it,’_ he decided, knowing he couldn’t escape it.

“I don’t know, Jess. I don’t really know the guy. He’s nice and all but, frankly, he’s a weird little dude, you know? Weird, and kind of brainy, which I’m not.”

Sam gave him a stern look. “Are you saying you’re not intelligent enough for him?”

“No… it’s just… he’s a writer, and not the Vonnegut kind. More like nerdy stuff. They teach his books in universities and shit.”

Jessica leaned back on her chair and crossed her arms, sending Dean a puzzled look. “You called him Cas before. Is it short for something?”

Dean shrugged, thinking back to how the man had introduced himself. “It’s something I’ve never heard before. Castiel…” He was startled when Jessica let out another squeal.

“Are you telling me you just spent the night with Castiel Novak? The magnificent author? The light of my life? Shut up, Sam,” she warned her boyfriend when she heard him cackling. “Dean, this is pure serendipity.”

“This is pure what, now?”

“Serendipity,” she said again, her eyes sparkling. “Chance, luck… _destiny_.”

Now weirded out, Dean turned to his brother who shook his head. “Sorry, Dean. You’re on your own,” he said with a shit-eating grin. “Welcome to my world.”

“I don’t wanna be in your world. She’s _your_ girlfriend, make her stop.”

“Dean, you don’t get it. Sammy and I, we’re going to his book signing today. I’ve had the tickets for months.” She turned to her boyfriend, an apologetic look on her face. “Babe, I know you’ll be disappointed, but you’re not invited anymore.”

He gave her a contrite look and nodded. “I understand,” he replied. Dean was the only one to see Sam’s mini victory fist-bump and he had to work hard not to laugh.

“Dean, you better go change because we’re leaving soon,” Jessica announced, giving his knee a squeeze. “We’ll get your man.”

“Huh… Jess?” Dean said, slightly confused. “I’m not going over there. We said our goodbyes, he’s going back home, we’re done.”

“You should have seen yourself when you came in, Dean. You were _glowing_.”

“She’s not wrong, Dean,” Sam added, only to be met with a dark glare.

“Dean, I’ve known you for years now and I’ve never seen you like this. Not even when you and Lisa were on your best days. Something special happened there, I just know it.”

“Are you sure it’s not just you being a creepy fangirl? You’re the one who’s in love with the guy. Don’t project your fantasies onto me.”

“Oh, honey… you went so much further than any fantasies I could have had. I didn’t even know he was into guys.”

Once more, Dean turned to his brother, giving him the most pleading look he could muster. “Sammy, talk to your girlfriend, would you? It was a one night stand, I can’t show up there.”

“Why not?” Sam asked, clearly not intending on helping him. “So what if you see him again? You said it yourself, you may have wanted to pursue the relationship if he had been from around here. And you know, New York isn’t _that_ far.”

“Not that far? Dude, it’s like fifteen hours away, if not more.”

Jessica perked up. “Pretty sure it’s not that long by plane.”

Before Dean could answer, Sam took the lead. “Dean is afraid of flying. You won’t get him on a plane.” A smug look on his face, Dean nodded to confirm his brother’s words.

“Then, he’ll be the one to come here. And I’m sorry but, as a writer, he could just move here. He doesn’t _need_ to be in New York to write, you know?”

For the first time since the start of that conversation, Sam seemed to want to pedal back a little. “Honey… they just met, it might be a bit early to think about either of them moving.”

“Finally,” Dean muttered, relieved. “Look Jess, he’s the first… hum… the first guy I ever slept with so… you know… it’d be like wanting to marry your high school sweetheart. That shit never works out.”

“My parents were high school sweethearts,” she replied, undeterred. “If it works, it works. Don’t you think you guys might deserve a chance? What if he’s the love of your life?”

Dean let his head fall on the table, dispirited. He knew that she couldn’t force him to go if he didn’t want to. But she had been able to put the idea in his head. He had already admitted to himself that it had been some of the best sex he’s ever had. And he also knew that if Cas hadn’t had obligations, they might have ended up spending the day together.

He groaned as his dick perked up at the thought of the two of them, naked and sweaty. “Fine,” he said, his voice muffled by the table. “I’ll go,” he confirmed as Jessica applauded and cheered him on.

“You’re making the right decision. Now go make yourself pretty.”

 

~ • ~

 

Castiel may have said he was moderately popular, Dean wouldn’t have thought there’d be that many people at the event. Not for shit like philosophy and whatnot. As the guests were let inside one of Kansas U’s lecture hall, Dean glared at Jessica. This was _not_ the setting for a book signing.

When she tried to pull him towards the front row, he stopped, making her turn around. “What the hell, Jess? This is not a book signing,” he whispered in her ear, not minding the annoyed huffs their halting caused.

“Of course it is,” she replied. “But Mr. Novak will read something from his last book and answer some questions first.”

Dean exhaled loudly as she pulled him forward. “No wonder Sam was glad you’d take me instead of him,” he mumbled, not loud enough for her to hear.

The first row had already been filled so Jessica found them seats in the second one, just in time too. Dean sat down, slouching as much as he could so he wouldn’t be seen by Cas. Sadly, the room’s layout didn’t make it easy for one to disappear.

It took another twenty minutes for the lights to dim. The only part of the room that remained well lit was the front, where the author would stand. It took another minute for a door in the front to open. The man Dean had briefly met that morning, Castiel’s brother, walked into the room.

As people applauded, he went to stand next to the podium. He tapped on the microphone in his hand, satisfied to hear the soft thumps come out through the speakers. “I’m not Castiel Novak, you can stop now.” Many laughed and the applause died down. “Hello, everyone. My name is _Gabriel_ Novak, Castiel’s agent and brother. I am very glad to say he now owes me fifty bucks… He didn’t believe me when I told him we’d be able to make students come to school on a Sunday.” Again, the crowd laughed.

“Even though you might already know, this is how this shindig will go down. Castiel will come out and read a chapter of latest book for you guys. Now, pay attention… you may learn a thing or two.” He looked around the room with a puckish smile. “You know all those fancy words he uses? There’s actually a right way to say them. Who knew, right?” Again, some laughs, but not as much. “After that, you’ll get a full hour to ask him questions. The third, and last act will be the actual book signing. If you don’t have your own copy of _Socrates and Other Soliloquies_ , or any of his earlier work, we’ll also be selling them.” 

He paused, again taking a second to size up the crowd. When Gabriel spoke, Dean could swear that he had been spotted and that the comment was for him. “Now guys, I urge you to buy a book, any book… Castiel will _not_ sign butts or any other body parts.” As the crowd laughed again, Dean tried to sink in his seat some more. “I think you’ve been patient enough. Ladies and gentlemen, please give a warm welcome to Mr. Castiel Novak.”

The room erupted in applause once more, some whistles being heard as the man appeared in the light. Dean’s throat constricted when he saw him approach the desk. Damn, he looked even better now than he had the night before. He wore dark gray chinos and a black button up, rather than the ordinary suit from last night. This right now was elegant and, yeah, fitted his form a little too well, in Dean’s opinion.

Dean squirmed on his seat as desire started blossoming in his belly. He took off his leather coat to fold it over his lap, not sure he’d be able to keep his dick in check. He saw Jessica notice and smirk at him. When he turned his attention back to the front, he saw Castiel’s eyes fixated on him. Dean’s heart dropped in his heels when the author looked away without any sign of recognition.

“Ladies and gentlemen, welcome to the signing of my latest book, _Socrates and Other Soliloquies_. I will be reading an excerpt, but I promise to keep it short. I am certain some of you are only here as companions. I wouldn’t want to make this day worst than it already is for them.”

Even Dean laughed. Sadly, he didn’t consider himself so much as a companion, more like a prisoner. Except that had to admit he was glad to be in Cas’ presence again. Even from afar.

“He totally saw you,” Jessica whispered in his ear.

“Yeah… and he’s probably freaking the hell out.”

“He doesn’t seem all that freaked out,” she said again before leaning away from him.

Castiel was true to his word, the reading not taking more than fifteen minutes. Dean tried to listen, he really did. Except he couldn’t find a way to be interested in what he said. All he could concentrate on was the voice of the man he had spent the night with. It was deep and even throatier than it was when they first met. Without wanting too, Dean found himself back in that  hotel room, submerged by last night’s images, sounds and smells.

He realized he had closed his eyes when he felt Jessica’s hand on his arm and her breath on his ear. “Dean, try and control yourself, would you? You look like you’re about to have an orgasm.”

Startled, Dean sat up in his seat, making sure the coat was still in place. He tried to rid his brain of everything Cas and his sultry voice.

“Yes, the young lady in the smurfs shirt,” he heard Gabriel say. Dean turned to his friend to see she had gotten up from her seat. Gabriel walked towards them to hand her the microphone. He glanced at Dean but ever so slightly.

“Yeah, hi Mr. Novak… my… my name is Jessica and… I just love you. I’ve read all your books and _Socrates and Other Soliloquies_ is by far my favorite,” she declared in a trembling voice.

“Thank you, Jessica. That is very nice of you to say. I am glad you appreciate my work.” As he answered, Castiel’s eyes stayed on Jess, not paying any mind to her friend. “Do you have a question for me?”

Jessica nodded, a bright smile lighting up her face. “Yes… I was wondering… are you married?” she asked, blushing. Some laughs and catcalls were heard around the room.

“All right, all right, settle down children,” Gabriel said in the microphone he had taken back from Jessica. “Anyone else has some book-related– ”

“It’s fine, Gabriel. I will answer Jessica’s question,” Castiel said, his eyes still on her. “No, I’m not married. Nor am I in a serious relationship. Not at this moment anyway,” he added, this time switching his attention over to Dean for half a second. He looked at Jessica again and smiled. “I hope my answer was satisfactory.”

Jessica smiled, giving him a vigorous nod. “You have no idea,” she said, loud enough to be heard without the help of device. “Thank you!”

When she sat back down, Dean gave her a dark look. “What was that about?” he said in a hiss. “That was not cool, Jess!”

“You heard him, right? He likes you just as much as you like him.”

“Would you shut up?” Dean said, sending a worried look to the people around them. But nobody seemed to be paying them any mind as Gabriel had given the microphone to someone else. “And what could ever make you say he likes me?”

“He looked at you when he said he didn’t have someone at the moment. That was nothing short of an invitation.”

“Or maybe, just maybe, he’s freaked out and wanted to make sure I know we’re _not_ together. Did you think about that?”

Jessica huffed, her eyes shooting to the ceiling. “No wonder you’ve been single for so long, Dean. You can’t see the signs even when they’re clear as day.”

Dean shook his head. “You’re wrong, Jess. Just… leave it, all right?”

She raised her hands as if to say ‘whatever’ and turned her attention back to the author. The hour went by fast, with most questions having to do with Castiel’s work rather than his personal life.

After the last question was answered, Gabriel walked back towards the front of the room to stand next to his brother. He grabbed him by the shoulders as he addressed the crowd.

“Thank you guys for your insightful questions. Castiel will be taking a short break while the staff prepares the signing area. You can start forming a line for the autographs using the left aisle. If you want to buy the book, please stand in line in the right aisle. A table will be set up in the next minutes. See you again soon.”

With his arm still around his brother’s shoulders, Gabriel walked them both to the side door while Jessica pulled Dean to stand in the left line. There were already many people standing and they had to climb a couple of rows up.

“This is so exciting,” Jessica said, holding onto Dean’s hand. “You’re sure you don’t wanna buy your own copy?”

Dean shook his head, showing her his brother’s book. “I’ll just have him sign Sam’s. It’s not my kind of stuff.”

“I bet it would be if it was an audiobook. Read by the author himself, of course,” she said in a low voice. Apparently not low enough because the two girls in front of them giggled.

He was about to tell Jess to shut up, yet again, when he felt someone tap on his shoulder. He turned around to see Gabriel standing next to them. _‘Shit, he’s gonna tell me to leave’_ , Dean thought, already bracing himself to have muscle men escort him out. Not that he had seen any.

“If you guys could please follow me,” Gabriel only said as he lead the way downstairs.

“Told you this was a bad idea, Jess. It’s your own fault that you’re getting kicked out,” Dean muttered as they followed the agent.

She took his hand and squeezed it. When she spoke, her tone was light and cheery. “They’re not kicking us out, Dean. Pretty sure Castiel just wants to see you.”

They ignored the gasps and giggles as they made their way towards the door where Cas had disappeared before. God only knew what people were thinking right now. They probably thought Cas had taken Jessica’s question for a come on and was responding to it. She was a beautiful woman, after all.

On the other side of the door, Castiel sat on a threadbare couch, drinking water from a bottle. A little flustered, Dean tried not to gawk at Castiel’s adam’s apple as he swallowed. The author turned to the newcomers and gave them a genuine smile. It helped ease Dean’s nerves a little.

“Why didn’t you tell me you were coming to my book signing, Dean?” he asked in a soft voice.

Before Dean could answer, Jessica interceded. “He wasn’t supposed to come. I was coming here with his brother but… then I heard… you know… anyway, I dragged him here,” she explained, sending a weary glance to Gabriel.

“Don’t worry, Gabe already knows. They actually met briefly this morning.”

“Hey there again, bucko,” the agent confirmed with a smirk and a military salute.

“Was the question your idea as well or was it Dean’s?” Castiel asked again, his attention solely on Dean who kept getting more uncomfortable by the minute. 

“It was my idea. I didn’t want to embarrass you.”

“You didn’t. But I think you may have embarrassed Dean.”

“Okay, that’s it… Let’s go, Jess… This is starting to feel like a deleted scene from the _Godfather_. I shouldn’t have come here, I’m sorry.”

Castiel got up and walked into Dean’s space, still smiling. “I don’t understand your _Godfather_ reference, but know that I’m not mad that you’re here, Dean. Quite the contrary, actually.”

“Told you,” Jessica declared as she elbowed her friend in the waist, making Castiel smile even wider.

He kept his eyes locked onto Dean’s when he spoke again. “Gabe, could you and Jessica leave us alone for the remainder of the intermission. I need to converse with Dean.”

“Of course, little brother, we’ll leave you two horndogs alone. Remember, Cassie… the room’s not soundproofed,” Gabriel said as he guided Jessica towards the door. 

She turned around, sending a worried look to Dean. “Are you okay with this?”

Whatever Gabriel had said, there was no way this would be anything but Cas wanting to tell him to lose his number. And maybe even warn him to stay away if he didn’t want to get served with a restraining order. Still, Dean nodded and gave Jessica a reassuring smile.

Gabriel gave her arm a delicate tug. “Come on, princess. I really don’t wanna see whatever’s about to go down.”

As soon as the door closed on them, Castiel moved forward and kissed a bewildered Dean. It was so far from what he had thought would happen. Still, he let himself respond to the embrace, his body catching fire again.

“Do you know how difficult it was to see you up there?” Castiel said as he let his mouth go, resting his forehead against Dean’s. “I’m so glad I had that podium to hide my erection.”

Dean chuckled, surprised by Castiel’s admission. “Dude, I almost came in my pants just hearing you read your thing. Even Jessica noticed.”

“I can’t go back there, not without…” Castiel said, letting the end of his sentence float between them.

“Are you asking for a blow-job?” Dean asked as he licked his lips.

“I don’t care what we do, as long as we do something,” Castiel breathed, crashing their mouths together again.

Dean took the lead, pushing their bodies until they reached the couch. Castiel let himself fall down like he had done that very morning but this time, Dean kneeled between his legs. They knew they didn’t have much time so teasing was not an option.

Castiel hadn’t pushed his pants down that Dean already had his mouth on him. He let out a raspy breath before hiding his face in the crook of his elbow. There was no way he could let a roomful of his readers hear him getting off. Still, he somehow found the thought arousing, his dick perking up in Dean’s mouth.

Working on Castiel with both his hand and mouth, Dean let out a low moan when he sent a hand to his own crotch. At that very moment, he wished he had an extra hand so he could play with Cas’ balls too. He took his mouth off of Cas, getting up to kiss him as he pushed both their bodies to lie on the couch.

He straddled him, working to open his own fly. He hissed as he let his aching flesh out of his pants. “Do me,” he said as he guided the author’s hand on him. He went back to kiss Cas and resumed stroking his dick.

“Give me a second,” Castiel said, letting Dean’s mouth go to spit in his own hand. He started kissing him again, now working on Dean with a damp hand. 

As they were getting close, Castiel took them both in his hand, stroking them simultaneously. Dean’s mind quickly went blank at the new sensations. 

“I’m… Cas… shit…” Dean tried to warn Castiel as he pushed himself away. He knew Cas couldn’t be going back out there with a spunk-covered shirt. Faster than lightning, Cas had his mouth on him as he came, sucking him dry. 

“Fuck… god you’re good,” Dean praised him. “Your turn,” he said, pushing the man backwards.

He resumed blowing Cas until he too came. Except Dean had never had a spurting dick in his mouth. To say that he almost choke was a fair assessment. But he worked through it, sucking and swallowing everything Cas had to give. Well, most of it anyway.

This time, Dean made sure to fasten his pants before sitting back on the couch, pulling up Cas so he’d be sitting next to him. He wiped his mouth with the back of his hand as he watched the other man make himself presentable again.

Satisfied, Castiel turned to Dean to grab him by the neck and kiss him, mixing their flavors together. “So now what?” he said under his breath, brushing his thumb over the short hair at the base of Dean’s skull.

“Dunno…” Dean answered with a shrug. “You’re still going back to New York. I don’t see this going anywhere with us so far apart.”

“I don’t see myself changing my whole life at this point in time. I don’t mean this in an insulting manner, I assure you. But we don’t really know each other.”

“Nah, I totally get it, Cas. I wouldn’t change my life either. Not now, anyway.” Dean leaned forward to give a soft kiss on Castiel’s lips. In the back of his mind, he still wished he wouldn’t have to let go of him. “I’m not sure I believe in long-distance relationships,” he said, because he felt he had to.

“I understand, I’m skeptical about it as well. It appears the stars are not working in our favor.”

Dean chuckled before kissing Castiel again. “Welcome to my life.”

They kept kissing for a little while, until they were interrupted by a knock on the door. “Cassie? Are you decent?” they heard Gabriel say as he opened the door by no more than a sliver.

“Yes, Gabriel, you can come in,” Castiel said as he got up, quickly followed by Dean.

The blond man walked in, this time without Jessica in tow.

“Where’s Jess?” Dean asked.

“She’s on the phone, with her boyfriend I think. So, are you ready Cassie? Got it all out of your system?” He turned to Dean and smirked. “Deano, you got a little something there,” he said, pointing to the corner of his own mouth.

Flustered, Dean wiped his mouth again, scolding himself to have been so careless.

“Gabriel, leave him alone. There’s nothing in the corner of your mouth,” Castiel explained to Dean, landing a comforting hand on his shoulder.

Dean glared at a cackling Gabriel, mad at himself to have fallen for it. Yeah, not having to see this asshole again had to be the silver lining to him and Cas never getting together.

“I need another minute, Gabriel,” Castiel answered. “We’re saying goodbye, I’d rather you wouldn’t be here,” he said again when his brother didn’t move.

“I thought you had done that already. Just, be quick, all right? Your fans are getting impatient.”

“Another minute is all I need,” Castiel confirmed, giving his brother a dismissive gesture. This time, he didn’t wait for him to be gone to turn to Dean and take his face into his hands.

“Dean… I know neither of us are in the best dispositions for entertaining a relationship, regardless of the distance between us.” Dean nodded, placing his own hand over Castiel’s. “But I keep thinking that something special has happened yesterday. Am I wrong, or do you feel it too?”

Not one to usually talk about his feelings, Dean still somehow felt compelled to share his every thought with Castiel. “You’re not wrong, Cas. But I honestly thought I was still on the high of my _first time_. That’s what this could be, right?”

“It wasn’t my first time, Dean,” Castiel answered with a confused eye-squint. “Is that all this is to you? A novelty?”

“Nah, man… well… I don’t know. All I know is I can’t seem to be able to keep my hands off of you.”

“I feel the same way. You don’t even know how much restraint I’m exerting right now.”

“I think I know, Cas,” Dean countered, pressing their crotches together.

“Stop, I can’t get out there aroused. We need to settle this.”

Dean nodded, letting Castiel go and taking a step back. “So what, you want to try the long-distance thing?”

“I don’t know… I wish I didn’t have to leave, quite frankly.”

“And I wish I could follow you… but wishing never does any good.”

“What type of work do you do?” Castiel asked in pensive tone.

“Huh… I work in a garage. The pay’s okay and I’m pretty good at it. Why?”

“Do you love your work?”

Dean shrugged, wondering where this was going. “I don’t hate it… My dad showed me the ropes and since I didn’t go to college, it’s probably one of the highest paying job I could ever get.”

“Would you take another job if it was offered to you.”

“What’s all this, Cas? I thought we were on the same page here… I’m not moving.”

“I’m not asking you to,” Castiel said, smiling. “I have been looking to hire an assistant for some time now. I’m certain it is something you could do. And the wages are pretty good.”

The look on Dean’s face wasn’t one Castiel had been expecting.

“What the hell? You wanna hire me as your  fuck toy? I may have a shitty job, but at least I’m not a whore. You can take your job offer and shove it up your ass, all right?” Dean grabbed his leather coat and pushed his brother’s book onto the author’s chest. “If you could sign this for Sam before I go, it’d be great.”

“But Dean, you misunderstand– ”

“Shut the hell up and sign the damn book.” 

Dean opened the door to find Gabriel and Jessica talking nearby. The smile on Jessica’s face dissolved when she saw him. She came to the door, clutching her own book over her chest.

“What’s wrong?” she asked before Dean grabbed the paperback and closed the door on her again.

“Here, this one’s for Jess… we’re leaving.”

“Dean, listen to me, would you?”

“I listened, and I answered. Just sign the damn books so I can get far away from you.”

With a contrite nod, Castiel took the second book from Dean’s hand and opened it to the first page. Dean made a point of looking away while Cas signed it. When he was done, he handed it back to Dean, along with Sam’s copy.

“Dean, I’m leaving tomorrow… please think about it.” He raised a hand in the hopes Dean would let him say what he wanted to say. “I can’t blame you for thinking the way you think, especially with the circumstances in which we met. But think about this… if I wanted a  fuck toy, as you put it, I could have called an escort service. I really need an assistant and if it’s not you, it will have to be someone else.”

Dean snorted, his lips pinched in disgust. “I bet it will.”

“I’m not offering you an easy job, Dean. You seem to think I only want you around so we can have intercourse. It’s a real position, with real tasks.”

“Cassie, it’s getting late,” they heard Gabriel call through the door. “Come on!”

“Another minute, Gabriel,” Castiel responded even though Dean was already walking to the door.

“You don’t need another minute. We’re done, Cas… it was nice and all, but now it’s getting weird. Just… let’s just leave it at that, all right?”

Defeated, Castiel pinched the bridge of his nose. “Very well. I am really sorry things had to end this way.

Dean didn’t answer and opened the door to leave, pushing both books in Jessica’s arms as he walked past her. “Dean, what’s going on?” she asked, scrambling to follow him.

“I’m going home, either you follow or you don’t,” Dean barked without looking back. Maybe he should have.

“What the hell, Jess?” he said in a yelp, holding the back of his head where one of her books had landed.

“First of all, don’t you ever talk to me that way again.” The blonde, usually peppy, was now looking at him with red hot fury in her eyes. “Second of all, I’m not leaving until you tell me what’s going on. I think you owe me an explanation after ditching me to go do whatever with Mr. Novak.”

Defeated, Dean hung his head low, wiping a hand on his face. “Fine… I’m sorry, but… I can’t do this here, all right?” he said in a low voice as he glanced at the crowd. “My car?”

“There’s a café nearby… I think you should at least buy me coffee if you’re gonna be ruining my whole day,” Jessica countered as she lead the way towards the exit.

Dean followed her without a word, picking up the book from the floor. Neither him or Jessica uttered a word as they made their way to the campus’ coffee shop. Even though there was a lot of people, Jessica found them a booth somewhat removed from the main area.

In a low voice, he ordered the grande vanilla latte and chocolate chips muffin she had asked for. He chose a simple black coffee for himself, not even tempted by the scrumptious looking peach pie displayed in the glass counter. By the time he went to sit with Jess, he found he wasn’t as pissed anymore.

“Ready to tell me what’s going on with you?” she said, her tone still on the dry side.

“Look, Jess… I’m sorry, all right? Things just didn’t end well, but it’s not important.”

She huffed, breaking her muffin in two. “That’s a given… but _why_? You guys looked very much… infatuated with each other.”

“I guess good sex’ll do that to you. But that’s all it was and then he got weird. He wanted me to come and “work” for him,” Dean said, complete with air quotes.

“To do what?”

“What do you think? He seems to think I’m some kind of whore.”

“I’m sure he doesn’t, Dean. What did he say exactly?”

As he drank his coffee, he thought back to the conversation. And however how he turned it around, it always sounded the same way to him. “He wanted to offer me a job as his assistant. I have a G.E.D. and work in a goddamn garage… what the hell could I ever do for him except swallow his load when he tells me to?”

Jessica didn’t answer, giving him a pensive look. “I think you may be right,” she said after a moment, shaking her head. “Or he panicked because he wanted to keep you close.”

“Like I said, he wanted to hire me as his whore.”

“I wouldn’t go so far,” Jessica countered, giving him a soft smile this time. “But I’d say he didn’t think it through. Not that you’re not intelligent or anything but… a writer’s assistant would have to help with the writing, proofing and research. I doubt that it’s something you’d like to do.”

“Pretty sure I wouldn’t… I’m not a nerd. If he really wants an assistant, pretty sure you’d be perfect for it.”

This time, Jessica gave him a wider smile. “Are you saying I’m a nerd?”

“Hell’s yeah… you and Sam are huge nerds.”

“Says the guy who watches _Star Trek_ anytime he has a chance.”

“ _Star Trek_ ’s a classic,” Dean replied, falsely offended. He was glad to see they seemed to be back in a good place. He really didn’t feel like getting another book thrown at him.

“Whatever you say, Dean. So now what? We go back home?”

“I have no reason to be here… I know you wanted to see him and all but, you got to meet him and your book’s signed so, do you still wanna stay? I could wait in the car or come and get you back later.”

Jessica opened her book, smiling again as she read the inscription Castiel had penned for her. “I guess there’s no point anymore. Thanks for having him sign it.”

“Didn’t give him a choice. I’m not that much of an asshole.” He winked at the young woman as he resumed drinking his coffee.

“So what now? You’re gonna see him again or…?”

“Nah, don’t think so, not after all this. I may be less pissed about it, but it was still a shitty thing for him to do.”

“Because it’s so shitty to wanna keep you around?”

Dean tried to laugh, but nothing came out. “I think I would have been less insulted if he had actually offered to be my sugar daddy. At least his intention would have been clear, you know?”

“I’m sure it’s all a big misunderstanding.”

“Maybe, but it’s too late now. Are you ready to go?” he said before drinking the last of his coffee.

She didn’t answer, closing the plastic lid on her coffee and getting up. Dean grabbed the tray to get rid of it and followed his friend outside. Again, they were silent on their way to the car, and as they drove back to Dean and Sam’s apartment. It was once parked that Dean spoke again, his voice a pleading one.

“Jess… just don’t tell Sam what happened, all right? I’m really not it the mood to spend the whole day talking about shit. Can you do this for me?”

With a soft hand on his forearm, she gave him a nod. “But you know he’s gonna ask questions, right?”

“Yeah, I know… I can handle him, don’t worry about it.”

“Fine. But Dean, if you ever want to talk about this, or anything else… you know I’m there for you, right?”

His smile was a bit on the sad side, but Dean appreciated the offer, leaning in to kiss her cheek. “I know… but I’m gonna be all right.”

 

~ • ~

 

It took a little over a month for Sam to confront his brother, tired of his brother’s behavior.

“Dean, what’s going on with you?” he said, his lips pursed. “I know something happened at that book signing and neither you or Jess will talk about it. I wouldn’t bother with it if you hadn’t being a major ass lately.”

“Nothing happened, Sam. Leave it alone, all right?”

“Bullshit! You’ve always been a bit of a slut but, man… you’ve been hooking up with someone different almost every day since then. You know bisexuality doesn’t mean you gotta have twice as much sex, right?”

Annoyed, Dean grabbed a beer from the fridge. “Jealous, are we?”

“You know I’m not. What I am is worried.”

“Don’t need to worry, Sammy, I’m fine… never better actually.” His phone’s text message alert chimed, grabbing Dean’s attention. “Huh… Benny wants to see me again,” he said as he typed something back.

“Who’s Benny?”

“Some guy I met at a club. We had a thing.”

Dismayed, Sam shook his head. “Are you being careful at least?”

“Come on, Sammy! Really, you’re gonna give _me_ the sex talk?”

“I don’t know where your head’s at anymore, so you know… I had to ask.”

Dean smiled, even though it was forced. “You didn’t _have_ to ask, but thanks anyway. I told you, don’t worry about me. I’m not stupid.”

When Dean’s phone chimed again, Sam noticed the change in his brother’s stance as he read the new message. Dean scowled at the device before putting it in his pocket.

“You’re not gonna answer?”

“Wrong number.”

Less than a minute later, Sam’s own phone vibrated as he received a message from Jessica.

**_Jessica_ ** _1:09 pm_  
_I’m coming over. Is Dean there?_

**_Sam_ ** _1:09 pm_  
_Yeah. Everything OK?_

**_Jessica_ ** _1:10 pm_  
_Yes. Don’t let him leave._

“Jessica’s coming over,” he announced to his brother.

“Why?”

Sam gave Dean a wide grin. “Dunno… probably ‘cause she misses me.”

“All right. I’ll get out of your hair.”

“You better stay, I think she wants to see you too.”

If she wanted to see him, that meant she wanted to talk. And if she wanted to talk, it couldn’t be about anything good.

“Thanks for the head’s up, man, I’m bolting!”

“Dean! What the hell’s wrong, seriously?”

“Nothing’s wrong. I just remembered I have to be somewhere that’s not here,” he said as he grabbed his coat and opened the door. He had to stop in his track when faced with two people standing in the hall.

“Hey, Jess! Didn’t think you’d be here this quick,” Sam said as he came to greet his girlfriend. He looked at the man standing next to her, taking a second to recognize him.

“Hmm… aren’t you–”

“What the hell is he doing here?” Dean cut his brother off, avoiding Castiel’s stare.

“He’s here to see you,” she answered, pushing the brown-haired man inside. “Come on, Sam. Let’s let them have a chat.”

Sam sent an apologetic glance to his brother but didn’t stay, letting Jessica pull him away. Dean was getting pissed but didn’t make Castiel leave, instead closing the door behind him.

He put his jacket on the coat rack before taking back his unfinished beer. “Want some?” he asked as he sat at the table. Castiel shook his head, coming to sit down with him. “I didn’t know you were back in town. Got another signing thing?”

“No, I came here to see you,” Castiel answered with honesty.

“You should have called, man. I would have told you it was a waste of time.”

“I wanted to apologize to you and I felt the need to do it in person.”

Dean snorted before taking a long pull of his beer, almost finishing it. He put back the bottle on the table and looked up so their eyes would meet. “Ah yeah? What for?”

“I’m sorry for making things weird between us, Dean. I never intended on doing that. I know you will never believe me, but I was truly offering you an assistant’s position. But it was a mistake to do so because… you are right when you say that my offer wasn’t all that innocent.”

“Told you. I’m not an idiot, Cas.”

“I never thought you were, Dean. But you need to understand it is not exactly what you think. I only offered you the job because I needed a reason to be close to you.”

“And how is that any different?”

Castiel leaned forward, taking Dean’s hand in his. To his own surprise, the other man didn’t move away. “I really felt something strong between us, Dean. And I wanted to know _you_ , not only your body but your heart and soul. And you were so adamant in your dislike of long-distance relationships…”

“You were too, if you remember correctly.”

“Indeed, I was… or so I thought. But then I met you and I couldn’t bear the thought of not seeing you again.”

Dean exhaled loudly, shaking his head. “We had plans to see each other again if we were in the same town or did you forget that?”

“Who knew when that could have happened? What if it never did?” Castiel squeezed Dean’s hand before speaking again. “I overreacted, and I’m sorry. I hate to think that you are mad at me. But don’t worry, I won’t be stalking you or anything. I just needed you to hear me.”

Dean nodded, getting up to grab two beers and open them. Even though Castiel had refused before, he took the offered bottle and drank from it. He grimaced at the taste but didn’t complain, only to see the corner of Dean’s mouth quirk up a little.

“How did you find me? Actually, how did you find Jess?

Castiel’s cheeks reddened, which Dean _didn’t find cute at all_.

“She was the one to find me, of all things. It appears you had told her about the assistant’s position and… well… she contacted Gabriel to offer her services.”

As he choke on his beer, Dean couldn’t decide if he was pissed or impressed by Jessica’s audacity. Not that ever intended on taking the stupid job, but she knew how he felt about the man himself. And now he’d be integrating his family’s tight circle?

“Okay… so what, her tasks include giving out her friend’s home addresses?”

“I didn’t hire her, Dean.”

“I bet you didn’t…”

It was Castiel’s time to let out a defeated exhale. “I didn’t hire her _yet_. I can imagine how you wouldn’t want to have me in such a close vicinity.”

“You’re asking me permission?”

“To some extent, I guess I am.”

Dean rubbed his eyes with his palms until they hurt as he tried to calm himself down. He didn’t want to be a douche and stand in the way of Jessica’s career, but he also didn’t want to have her move and take Sam with her.

“She’d have to go live in New York?” he asked, scared of the answer to come.

“Not if she doesn’t want to. Thanks to the Internet, most of her tasks could be handled remotely. I’d probably need her to come meet me from time to time but… no moving is necessary.”

Relieved, Dean nodded, knowing that even if the answer had been yes, he’d never forgive himself to try and control Jessica life or his brother’s. Anyway, he knew that if they’d leave, he couldn’t resist following them.

“It’s not my place to give her permission to work for you, man. She’s her own person and she certainly doesn’t owe me shit.”

“I agree… but it was she who wanted me to ask you. And of course, I agreed. I wouldn’t want you to be uncomfortable if we were to cross paths again.”

“Thanks, but like I said, it’s her call. I couldn’t stand in her way. And don’t worry, I’ll be a perfect gentleman if I ever see you again.”

They stayed silent for a while, looking at anything but each other. Unnerved, Castiel got up and mumbled his goodbyes as he went to the door. Before he could open it, Dean talked again.

“I wouldn’t mind having you close, Cas,” Dean said under his breath. Castiel still heard him, turning around to look at him.

“That’s not the impression I gathered from our last encounter. Or even from the last ten minutes.”

“Well… I was weirded out, man. We had just met.”

“I’m aware of that, yes. Again, I apologize for making you uncomfortable. I sometimes wish I could go back in time, but I can’t.”

“Yeah, that’d be nice,” a wistful Dean replied.

“I take that you regret ever answering my ad?”

Dean’s head shot up, his eyes wide in shock. “What? No, man, not at all. If anything, it’s the last good decision I’ve made. I can’t count how many mistakes I’ve made since then.”

“Was refusing my offer one of those mistakes?” Castiel asked in a soft voice as he walked back towards Dean.

“I’d still say no, but I wouldn’t be an ass about it. You weren’t the only one to overreact, you know.”

Castiel nodded and he got closer, stopping right in front of Dean instead of sitting back on his chair. He quirked an eyebrow at Dean before sitting down on his lap.

“Is this all right?” he asked, his breath warm on Dean’s ear.

With a trembling nod, Dean caved, knowing it would be futile to try and resist. But when Castiel tried to kiss him, Dean avoided his lips.

“Look, Cas… I gotta tell you. Those things I regret… I’ve tried real hard to forget about you.”

“You don’t owe me any explanations, Dean,” Castiel assured him before kissing his neck. “I would be lying if I said I didn’t try to do the same.”

“I still… I’ve been with other people since you. Mostly guys, but girls too… shit, none of them ever made me feel as good as you did.”

Castiel let out a pleased humm. “Same for me, except for the girl part. I realized a long time ago that men were what did it for me.” He kept mouthing at Dean’s neck, sucking a bruise.

“I… I’d still like both but… not if I got you,” he admitted, desire making him woozy.

“I’m glad you think so, Dean,” Castiel said, cradling Dean’s face with both his hands and forcing their eyes together. “I was so afraid you’d never want to see me again.”

“If you hadn’t come here, I would not have tried to find you.”

“I know.”

“Don’t you mind?”

Castiel shrugged, pressing a soft kiss over Dean’s lips. “You didn’t have anything to apologize for.”

“Yeah, Cas, I did. I still do,” Dean said before kissing him back. “I’m sorry for making a scene back there. I can’t say it didn’t sound like you were trying to make me your _Pretty Woman_ , but I could have handled it better.”

“I never intended to imply that you were a woman, Dean,” Castiel said, making Dean laugh.

“Dude, I mean the movie. Julia Roberts as a prostitute and Richard Gere hiring her for the week-end?”

Castiel squinted his eyes, not finding the explanation helpful. “To be fair, I intended on hiring you for more than a week-end. Like I said, it was a real job offer. Misguided, but not less true.”

Without answering, Dean kissed the man again, this time with clear intent behind it. He had a fleeting thought for his brother and girlfriend, hoping they weren’t just waiting in the hall. He soon found that he didn’t care as Castiel’s hands snaked underneath his t-shirt. Whatever was about to happen, he was very much down with it.

“We might want to move to your bedroom if we don’t want to scar your brother for life,” Castiel whispered on his lips, once again making Dean wonder if he could read minds.

“Hold on tight,” he said as he got up from the chair. With Castiel clinging to him, he walked them both towards the end of the hall, glad there weren’t stairs to climb this time.

His room was a bit dark even though it was midday, the blinds still closed. Neither of them seemed to care, too busy rediscovering each other to think about anything else.

Unlike the first time they were together, everything went fast. They didn’t tease one another by undressing slowly, instead tearing their clothes off and throwing them all over the room. With Castiel on his back, Dean took control and kissed his way down until he had his dick in his mouth.

“Oooh… Dean…” Castiel said in a hiss, bunching his fingers in the sheets. He choked on air when he felt his dick slide down Dean’s throat. “Oh dear… lord… uhg…How…” He almost wept when Dean let him go, sliding his tongue on his whole length and teasing the slit.

“Told you I tried to forget you,” Dean said in a throaty voice, licking his lips. 

He moved back up to kiss Castiel, licking his lips until he was let in. They both moaned as Dean moved his hips down, sliding his already hard dick along Castiel’s. 

“Fuck me,” Castiel murmured in Dean’s mouth, shivering. 

“Yeah, okay… shit, you’re hot…”

Not letting Cas’ mouth go, Dean scrambled to find a condom and lube in his nightstand. He sat up with a huff, unable to find what he was looking for. Of course, they were all the way in the back of the drawer.

“Give me the lube,” Castiel asked, already with two fingers up his own ass. “I kind of hoped…” he explained to a surprised Dean, a little sheepish. 

But Dean’s surprise didn’t last, his expression switching to a predatory one. He squirted a dollop of lube in Castiel’s waiting hand then unwrapped the condom. He couldn’t look away from Castiel opening himself as he rolled down the latex protection and covered it in lube. 

“Come on,” he groaned, his eyes clouded by lust. 

Castiel let out a fait mewl as he took his fingers out, locking his own lustful gaze onto Dean’s. “I need you… just… oh yessss,” he almost screamed when Dean pushed himself in. He didn’t bottom out right away, not wanting to hurt his lover, but Cas wasn’t as patient. 

“Just move,” he said in a hiss, grabbing Dean’s ass to pull him forward.

If their first times together were almost romantic, this right now wasn’t. It was rough, savage, bordering violent. They pretty much came together, the stuttering of Dean’s hips and pulsing of his dick bringing Castiel over the edge.

Dean fell over, his ragged breathing warm on Castiel’s neck. He wiggled out of Cas, then wrapped himself over him. “That was… awesome,” he said, breathless.

“It was… you are an exquisite lover,” Castiel said as he kissed Dean’s forehead.

“Why is it so good? It’d be so much simpler if it was just okay, you know?”

“I know… I feel the same way.”

Dean hummed, brushing his lips on Castiel’s stubble. “Now what?”

“Do you really want to talk about this now?”

With a small laugh, Dean shook his head and kissed his lover’s cheek. “Nah… later.”

 

~ • ~

 

It was dinner time when Sam and Jessica came back to the apartment with bags of chinese takeout. Castiel and Dean were in the living room watching _The Godfather_. Well, it must have been what they intended to do but instead were making out, tangled up together on the couch.

“Come on guys, we got chinese,” Sam called as he emptied the bags on the small table.

Dean receded from Castiel’s hold to answer his brother. “What’s the occasion?”

“Sam told me you may need something special after seeing Cas, would the outcome be positive or not.” Jessica had walked in the living room, a pleased smile on her lips. “So… do I get the job?” she asked Castiel with a wink.

“You are indeed hired as my new assistant. Your first task was executed tremendously well.”

“If I may say so myself, I think you’re the one who looks executed,” she said before going back to the kitchen, cackling.

Dean held onto Castiel a bit tighter, his lips grazing his neck as he spoke. “I sometimes wish I could hate her, you know?”

“I don’t think anybody could.”

They both laughed, holding onto each other even tighter now. It was like they feared letting go, scared the reality of things would catch up with them.

“I still wish I could stay, or that you could follow me,” Castiel murmured, his breath warm puffs on Dean’s stubbled jaw.

“I know, I do too… I think we just need some time to figure things out.”

Castiel nodded, his own stubble scratching his younger lover’s. “At some point, we _will_ have to get to know each other. We can’t base this purely on sex.”

“Great sex, Cas… but yeah, I get it. I guess being away most of the time should help. Unless we just do the phone or webcam sex thing.”

“Come on, guys… it’s getting cold,” they heard Sam say again, sounding annoyed now.

“Chinese is good cold, give us a sec,” Dean yelled back.

Castiel snorted, retreating from Dean’s hold. “No, it’s not. Let’s just go and honor the meal.”

Dean let himself be hauled up and pushed out of the living room. Jess and Sam hadn’t waited for them, their plates already full of everything from eggrolls to orange chicken. The couple sat down without untangling their hands, to Jessica’s evident pleasure.

“So, are you guys dating now?” she asked, not minding her boyfriend’s wary gaze.

Both men smiled and turned to each other instead of answering. Their eyes locked together for a little while as if they were in a silent conversation. And maybe they had been because Castiel nodded and turned his attention back to Jessica.

“We are willing to try the long-distance thing, for the time being anyway. I can safely say that I intend on being exclusive to Dean from this moment on. Not that I am asking him to do the same,” he added, looking at Dean again.

“I don’t want nobody else, man. As long as we’re trying this thing, you’re my only one.”

“Aww,” Sam and Jessica purred in unison as the men kissed. 

But of course, the cuteness of it all was short lived. For that, they had Sam to thank as he made a point of mock-puking like the bratty overgrown child that he was.

And for once in his life, Dean could see blue skies ahead.

Electric blue skies.

 

 

~ • ~  Fin  ~ • ~

**Author's Note:**

> Pretty much everything is NOT copyrighted by me, except for the drawing. And the story, to some extent… anyway, you know how that works, right?
> 
> I really hope you liked it… if so, please don’t hesitate to tell me… and even if you didn’t, you can still tell me. I’ll only get better if I know what I do wrong! ;)


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